Composition for controlling harmful bio-organisms and method for controlling harmful bio-organisms using the same

ABSTRACT

A composition for controlling harmful bio-organisms comprising (a) at least one imidazole compound represented by formula (I):  
                 
wherein R represents a lower alkyl group or a lower alkoxy group; and n represents an integer of 1 to 5, as an active ingredient, and (b) at least one inorganic phosphorus compound and/or at least one fungicide for Phycomycetes as an active ingredient or (c) a spreader as an activity-enhancing ingredient, and a method for controlling harmful bio-organisms comprising applying the composition for controlling harmful bio-organisms onto harmful bio-organisms.

TECHNICAL FIELD

This invention relates to a composition having markedly enhancedcontrolling effects on harmful bio-organisms, especially curative and/orpreventive effects on plant diseases, and are useful in agriculture andhorticulture; a method for controlling harmful bio-organisms using thecomposition; and a method for enhancing the harmful bio-organismcontrolling effects of a harmful bio-organism controlling agent.

BACKGROUND ART

With reference to a combination of active ingredients (a) and (b) usedin the present invention (hereinafter described), EP Patent No. 298196teaches that the imidazole compound used in the present invention asactive ingredient (a) is useful as a harmful bio-organism controllingagent, referring to the possibility of using the compound in combinationwith other fungicides if desired. EP Patent No. 298196 adds that acombined use of an imidazole compound structurally similar to theimidazole compound used in the present invention as active ingredient(a) with other fungicides, such as cyanoacetamide compounds (e.g.,1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea) and organic chlorinecompounds (e.g., tetrachloroisophthalonitrile), brings about enhancedeffects. Furthermore, EP Patent No. 337103 discloses a harmfulbio-organism controlling agent containing at least one imidazolecompound structurally similar to the imidazole compound used in thepresent invention as an active ingredient and at least one activeingredient selected from a cyanoacetamide compound, an organic chlorinecompound (including tetrachloroisophthalonitrile), a phenylamidecompound (including methylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate), a cinnamic acidcompound, a copper compound, and an organophosphorus compound (includingFosetyl-Aluminum).

Reviewing these patents in view of the present invention, they do notdescribe nor suggest a combination of the imidazole compound as activeingredient (a) and an inorganic phosphorus compound, a β-methoxyacrylatecompound or an oxazolidinedione compound. Neither do they describe norsuggest the pronouncedly excellent controlling effects which may bepossessed by a composition comprising the imidazole compound as oneactive ingredient and at least one member selected from the groupconsisting of a cyanoacetamide compound, an organic chlorine compound, aphenylamide compound, a cinnamic acid compound, a copper compound, andan organophosphorus compound as the other active ingredient.

With respect to a combination of active ingredient (a) andactivity-enhancing ingredient (c) (hereinafter described), EP Patent No.298196 describes usefulness of the imidazole compound of the presentinvention as a harmful bio-organism controlling agent, teaching thatthis compound can be formulated into various forms together withadjuvants. JP-A-Heisei-3-11003 (the term “JP-A” as used herein means an“unexamined published Japanese patent application”) discloses a methodfor controlling harmful bio-organisms comprising applying an aqueousdispersion containing at least one of the imidazole compounds of thepresent invention and a sorbitan higher fatty acid ester surface activeagent.

The imidazole compound represented by formula (I) and many otherconventional harmful bio-organism controlling agents have their severalcharacteristics in the controlling effects. Some produce insufficienteffects on some harmful bio-organisms, or some are less effective incuring than in prevention, or some have relatively short duration inresidual effect. Therefore, cases are sometimes met with in which theircontrolling effects on harmful bio-organisms are insufficient inpractice in some uses. Further, although the imidazole compound offormula (I) exhibits excellent fungicidal effects on Phycomycetes, ittends to fail to produce sufficient curative and/or preventive effectsdepending on the situation of the development of a disease. From thisaspect, too, enhancement has been desired.

On the other hand, in practical application of a harmful bio-organismcontrolling agent comprising the imidazole compound of formula (I), itis desirable to minimize the amount of the compound to be used for costsaving while trying to control a plurality of harmful bio-organismsdifferent in kind, the time of disease breakout or the time ofoccurrence as much as possible. Further, while the harmful bio-organismcontrolling agent containing the imidazole compound of formula (I) as anactive ingredient is particularly excellent in preventive effect, it hasbeen-demanded to enhance its curative effect.

DISCLOSURE OF THE INVENTION

The inventors of the present invention have studied in order to settlethe above-mentioned problems and have found as a result that a combineduse of the imidazole compound of formula (I) as active ingredient (a)and a specific compound as active ingredient (b) produces unexpectedresults such that the respective amounts of the compounds can be reducedor the respective control spectra are broadened as compared with theirindividual use. They have also found that a combined use of activeingredient (a) with activity-enhancing ingredient (c) brings aboutmarked enhancement in controlling effect, particularly curative effect,as compared with the use of active ingredient (a) alone, thereby makingit possible to reduce the amount of active ingredient (a) The presentinvention has been reached based on these findings.

The present invention relates to a composition for controlling harmfulbio-organisms comprising

-   -   (a) at least one imidazole compound represented by formula (I):    -   wherein R represents a lower alkyl group or a lower alkoxy        group; and    -   n represents an integer of 1 to 5,        as an active ingredient, and    -   (b) at least one inorganic phosphorus compound and/or at least        one fungicide for Phycomycetes as an active ingredient or    -   (c) a spreader as an activity-enhancing ingredient.

BEST MODE FOR PRACTICING INVENTION

In formula (I), the lower alkyl group or the alkyl moiety of the loweralkoxy group as represented by R includes an alkyl group having 1 to 6carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl or hexyl,which may have either a straight chain or a branched chain. When n is 2or greater, the plural Rs may be the same or different.

The imidazole compounds represented by formula (I) include the followingcompounds:

-   4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methylphenyl)imidazole    (Compound No. 1);-   4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-methoxyphenyl)imidazole    (Compound No. 2);-   4-chloro-2-cyano-1-dimethylsulfamoyl-5-(4-ethylphenyl)imidazole    (Compound No. 3); and-   4-chloro-2-cyano-1-dimethylsulfamoyl-5-(3-methyl-4-methoxyphenyl)imidazole    (Compound No. 4).

The imidazole compounds of formula (I) can be prepared by knownprocesses disclosed, e.g., in EP Patent No. 298196 or EP-A-705823.

The inorganic phosphorus compounds as active ingredient (b) includephosphoric acid, phosphorous acid, hypophosphorous acid, condensedphosphoric acid, condensed phosphorous acid, and salts thereof. Thesalts include those with light metals (specific gravity: less than 4),such as alkali metals, alkaline-earth meals, aluminum, etc.; heavymetals (specific gravity: 4 or more), such as zinc, copper, nickel,manganese, etc.; and substituted or unsubstituted ammonium salts.

Salts of phosphoric acid include primary phosphates (e.g., sodiumdihydrogenphosphate, potassium dihydogenphosphate, aluminumdihydrogenphosphate, ammonium dihydrogenphosphate, calciumdihydrogenphosphate), secondary phosphates (e.g., disodiumhydrogenphosphate, dipotassium hydrogenphosphate, diammoniumhydrogenphosphate, dimagnesium hydrogenphosphate), and tertiaryphosphates (e.g., trisodium phosphate, tripotassium phosphate, zincphosphate, aluminum phosphate, ammonium phosphate, ammonium magnesiumphosphate, magnesium phosphate, calcium phosphate).

Salts of phosphorous acid include primary or secondary phosphites (e.g.,sodium primary or secondary phosphite, potassium primary or secondaryphosphite, calcium primary or secondary phosphite).

Salts of hypophosphorous acid include sodium hypophosphite, bariumhypophosphite, and calcium hypophosphite.

Condensed phosphoric acids and salts thereof include polyphosphoricacids (e.g., pyrophosphoric acid), and polyphosphates (e.g., sodiumpyrophosphate, calcium pyrophosphate, disodium dihydrogenpyrophosphate).

Condensed phosphorous acids and salts thereof include polymetaphosphoricacids (e.g., trimetaphosphoric acid, tetrametaphosphoric acid), andpolymetaphosphates (e.g., sodium trimetaphosphate, sodiumtetrametaphosphate, sodium hexametaphosphate).

The fungicides for Phycomycetes which can be used as active ingredient(b) include:

β-methoxyacrylate Compounds

-   (e.g., methyl    (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,-   methyl (E)-methoxyimino[α-(o-tolyloxy)-O-tolyl]acetate);

Oxazolidinedione Compounds

-   (e.g.,    3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione);

Cyanoacetamide Compounds

-   (e.g., 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea (common name:    Cymoxanil));

Organic Chlorine Compounds

-   (e.g., tetrachloroisophthalonitrile (common name: Chlorothalonil),-   pentachloronitrobenzene (common name: Quintozen));

Phenylamide Compounds

-   (e.g., methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (common    name: Metalaxyl),-   2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)aceto-2′,6′-xylidide (common    name: Oxadixyl),-   (±)-α-2-chloro-N-(2,6-xylylacetamide)-γ-butyrolactone (common name:    Ofurace),-   methyl N-phenylacetyl-N-(2,6-xylyl)-DL-alaninate (common name:    Benalaxyl),-   methyl N-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate (common name:    Furalaxyl),-   (±)-α-[N-(3-chlorophenyl)cyclopropanecarboxamide]-γ-butyrolactone    (common name: Cyprofuram));

Cinnamic Acid Compounds

-   (e.g.,    (E,Z)-4-[(3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine    (common name: Dimethomorph));

Copper Compounds

-   (e.g., organic or inorganic copper fungicides); and

Organophosphorus Compounds

-   (e.g., aluminum tris(ethyl phosphonate) (common name:    Fosetyl-aluminum),-   O-2,6-dichloro-p-tolyl-O,O-dimethyl phosphorothioate (common name:    Tolclofosmethyl),-   (R,S)-S-(R,S)-sec-butyl-O-ethyl-2-oxo-2-thiazolidinyl    phosphonothioate,-   S-benzyl diisopropyl phosphorothioate (common name: Iprobenfos),-   O-ethyl diphenyl phosphorodithioate (common name: Edifenphos),-   ethyl    2-diethoxythiophosphoryloxy-5-methylpyrazolo(1,5-a)pyrimidine-6-carboxylate    (common name: Pyrazophos))

Of these,(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate(hereinafter referred to as “compound (a)”), methyl(E)-methoxyimino[α-(o-tolyloxy)-O-tolyl]acetate (hereinafter referred toas “compound (b)”), and3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione(hereinafter referred to as “compound (c)”) are described in BrightonCrop Prot. Conf. Pests and Diseases, pp. 435-443 (1992), ibid, pp.403-410 (1992), and ibid, pp. 21-26 (1996), respectively.

Of the above-described organic chlorine compounds,tetrachloroisophthalonitrile is preferred. Of the phenylamide compounds,methyl N-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate is preferred. Ofthe organophosphorus compounds, aluminum tris(ethyl phosphonate) ispreferred. Of the copper compounds, an inorganic copper fungicide ispreferred.

The inorganic or organic copper fungicides as referred to the aboveinclude fungicidal preparations containing chemicals (such asfungicides, etc.) other than active ingredients (a) and (b) in additionto the copper compound.

The inorganic copper fungicides include those containing copperoxysulfate as an active ingredient, such as Sanpun Bordeaux (trade name,produced by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.)and Sanpun Bordeaux Dust DL (trade name, produced by Dai-ichi NoyakuK.K. and Hokko Chemical Industry Co., Ltd.); those containing copper (I)oxychloride as an active ingredient, such as San Bordeaux (trade name,produced by Sankei Chemical Co., Ltd.), Deutch Bordeaux A (trade name,produced by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co., Ltd.),Do-cal Wettable Powder (trade name, produced by Yashima ChemicalIndustry Co., Ltd.), Do-jet (trade name, produced by Nissan ChemicalIndustries, Ltd.), etc.; those containing cupric hydroxide as an activeingredient, such as Kocide Bordeaux, Kocide DF, Kocide SD (trade names,all produced by Griffin), etc.; and those containing anhydrous copper(II) sulfate, such as Gandie Wettable Powder (trade name, produced byAgro-Kanesho Co., Ltd.), etc.

The fungicidal preparations containing the inorganic copper fungicideand chemicals (such as fungicides, etc.) other than ingredients (a) and(b) include a Bordeaux mixture containing basic copper calcium sulfate;copper-sulfur fungicides, such as Engei Bordeaux (trade name, producedby Sankei Chemical Co., Ltd.), etc.; copper-validamycin fungicides;copper-validamycin-fthalide fungicides; copper-pyrifenox fungicides;copper (I)-vinclozolin fungicides; copper-fthalide fungicides;copper-procymidone fungicides, such as Scletane Wettable Powder (tradename, produced by Hokko Chemical Industry Co., Ltd.); copper (I)-fosetylwettable powders; copper-metalaxyl fungicides, such as Ridomil CopperWettable Powder (trade name, produced by Nihon Nohyaku Co., Ltd.);iprodione copper (I) fungicides, such as Daisedo Wettable Powder (tradename, produced by Yashima Chemical Industry Co., Ltd.); iminoctadienetriacetate-copper fungicides; oxadixyl copper (I) fungicides; oxolinicacid-copper fungicides; kasugamycin-copper fungicides, such as KasuminBordeaux Dust 3DL (trade name, produced by Hokko Chemical Industry Co.,Ltd.), Kasumin Bordeaux (trade name, produced by Dai-ichi Noyaku K.K.and Hokko Chemical Industry Co., Ltd.), etc.; dithianone copper (I)fungicides; streptomycin-copper fungicides, such as Do-Stomy WettablePowder (trade name, produced by Nihon Nohyaku Co., Ltd.), etc.; sodiumhydrogencarbonate-copper fungicides, such as G-Fine Wettable Powder(trade name, produced by Yashima Chemical Industry Co., Ltd.); andcopper-organocopper fungicides, such as Oxy Bordeaux (trade name,produced by Sankyo Co., Ltd.), Kinset Wettable Powder (trade name,produced by Agro-Kanesho Co., Ltd.), Kinset Wettable Powder 80 (tradename, produced by Agro-Kanesho Co., Ltd.), etc.

Of these inorganic copper fungicides, it is particularly preferred touse those containing one or more active ingredients selected from thegroup consisting of cupric hydroxide, copper oxysulfate, copperoxychloride, anhydrous copper (II) sulfate, and basic copper calciumsulfate.

The organic copper fungicides include 8-hydroxyquinoline copperfungicides, such as Quinone-do Wettable Powder 40 or 80 (trade name,produced by Agro-Kanesho Co., Ltd.), Quinone-do Granules (trade name,produced by Agro-Kanesho Co., Ltd.), Quinone-do Flowable (trade name,produced by Agro-Kanesho Co., Ltd.), Oxine-copper (I) Wettable Powder(trade name, produced by Tomono Agrica Co., Ltd.), Oxine-copper (I)Wettable Powder 75 (trade name, produced by Tomono Agrica Co., Ltd.),Oxine-copper (I) Wettable Powder 80 (trade name, produced by TomonoAgrica Co., Ltd. and Nissan Chemical Industries, Ltd.), Oxine-copper (I)Flowable (trade name, produced by Tomono Agrica Co., Ltd. and NissanChemical Industries, Ltd.), Doquline Wettable Powder 80 (trade name,produced by Nihon Nohyaku Co., Ltd.), and Dokirin Flowable (trade name,produced by Nihon Nohyaku Co., Ltd.), etc.; copperhydroxynonylbenzenesulfonate fungicides such as Yonepon (trade name,produced by Yonezawa Kagaku K.K.), etc.; copper (II)bis(ethylenediamine)bis(dodecylbenzenesulfonate) fungicides, such asSanyol (trade name, produced by Otsuka Chemical Co., Ltd. and YonezawaKagaku K.K.), etc.; and copper terephthalate fungicides.

The fungicidal preparations containing the organic copper fungicide andfungicides other than ingredients (a) and (b) include iprodione(I)-organocopper fungicides, oxolinic acid-organocopper fungicides,captan (I)-thiuram-organocopper fungicides, captan (I)-organocopperfungicides, dithianon (I)-organocopper fungicides,streptomycin-organocopper fungicides, thiabendazole (I)-organocopperfungicides, fenarimol (I)-organocopper fungicides, machineoil-organocopper fungicides, and guazatine (I) iminoctadine-organocopperfungicides.

A spreader is used as activity-enhancing ingredient (c). Examples of thespreader for use in the present invention include surface active agents(exclusive of sorbitan higher fatty acid esters), paraffin oil, animaland/or vegetable oil, and mineral oil. In general, spreaders are notdefinitely classified. Some of animal and/or vegetable oil, and mineraloil serve as surface active agents, and there are some spreaders calledstickers that cannot be classified clearly. Any spreader thatappreciably enhances the physical properties of the imidazole compoundof formula (I), such as fixing properties, penetrability, spreadability,and stomatal flooding properties, to enhance the effects of the compoundcan be used in the present invention. Typically, the physical propertiesof the imidazole compound of formula (I) could be enhanced by thespreader to bring about such an effect that equal harmful bio-organismcontrolling effects are obtained with a lesser amount of the compound.Of the above-described spreaders preferred are surface active agents(exclusive of sorbitan higher fatty acid esters), animal and/orvegetable oil, and mineral oil. Still preferred are nonionic surfaceactive agents (exclusive of sorbitan higher fatty acid esters), animaland/or vegetable oil, and mineral oil.

Suitable nonionic surface active agents which can be used asactivity-enhancing ingredient (c) include polyoxyethylene alkyl ethers,polyoxyethylene alkylphenyl ethers, polyoxyethylene aryl ethers,polyoxyethylene glycol alkyl ethers, polyoxyethylene fatty acid esters,polyoxyethylene polyol fatty acid esters, polyoxyethylene fatty acidamides, amine N-oxides such as Aromox C/12W (trade name, produced byAkzo Chemie), polyoxyethylene alkylamines, glycerol fatty acid esters,silicone surface active agents, polyoxyethylene alkyl thioetherpolyphosphate surface active agents such as Reider (trade name, producedby American Trading Company), higher alcohol sulfuric acid esters, anddialkylsulfosuccinates. Among these, preferred are polyoxyethylene alkylethers, polyoxyethylene alkylphenyl ethers, polyoxyethylene fatty acidesters, polyoxyethylene fatty acid amides, silicone surface activeagents, higher alcohol sulfuric acid esters, and dialkylsulfosuccinates.Still preferred are silicone surface active agents, polyoxyethylenealkylphenyl ethers and polyoxyethylene fatty acid esters. Siliconesurface active agents, especially Dyne Amic (trade mark, produced bySetre Chemical) and KINETIC (trade mark, produced by Setre Chemical),and SILWETT L-77 (produced by Witco), and SLIPPA (produced by Interagro)are particularly preferred.

Specific examples of preferred nonionic surface active agents are listedin Table 1 below. Additionally polyoxyethylene polysilane ether (a kindof silicone surface active agents), Renex 36 (trade name,polyoxyethylene alkyl ether produced by Bayer AG), Crop Oil Extra (tradename of a polyoxyethylene alkylphenyl ether produced by Kalo, Inc.),Ortho X-77 Spreador (trade name, produced by Chevron Chemical Company),and COOP Spreader Activator (trade name, produced by Formland Industry)are also included in usable nonionic surface active agents. TABLE 1Nonionic Surface Active Agents Trade Name No. Kind Designation(Manufacturer) 1 Polyoxyethylene Genapol LRO Fluid alkyl ether (HoechstAG) 2 Polyoxyethylene ethylene oxide adduct Lutensol TO 7 alkyl ether ofiso-C₁₃ oxo alcohol (BASF AG) 3 C₁₀ oxo alcohol + ethylene oxide adductLutensol ON 60 ethylene oxide of C₁₀ oxo alcohol (BASF AG) 4Polyoxyethylene AGRAL 30 (ICI alkylphenyl Agrochemicals) ether 5Polyoxyethylene 90% nonyl phenoxy AGRAL 90 (ICI alkylphenylpolyethoxyethanol Agrochemicals) ether 6 Polyoxyethylene nonirfenplAGRAL PLUS (ICI alkylphenyl polietilenglicol eter Agrochemicals) ether 7Polyoxyethylene ARKOPAL N-100 alkylphenyl (Hoechst AG) ether 8Polyoxyethylene ethylene oxide Citowett (BASF AG) alkylphenyl condensateor CITOWETT ether 9 Polyoxyethylene Genapol X-60 alkylphenyl (HoechstAG) ether 10 Polyoxyethylene ethoxylated fatty Frigate ® (ISKalkylphenyl amine Biotech Europe, Ltd.) ether 11 polyoxyethylenepolyoxyethylene SOPROPHOR ® BSU aryl ether tristyrylphenyl ether(RHÔNE-POULENC) 12 polyoxyethylene polyoxyethylene KUSARINO (Nihonalkylphenyl octylphenyl ether Nohyaku Co., Ltd.) ether 13polyoxyethylene Noigen EA110 alkylphenyl (Daiichi Kogyo ether SeiyakuCo., Ltd.) 14 polyoxyethylene polyethylene glycol TOKUSEI RINOalkylphenyl alkylphenol ether (Nihon Nohyaku ether + lignin (20%) +lignin Co., Ltd.) sulfonate sulfonate (12%) 15 polyoxyethylenepolyoxyethylene RHODASURF ® fatty acid aliphatic alcohol 860/p ester(RHÔNE-POULENC) 16 polyoxyethylene polyoxyethylene D-3605 (Takemotofatty acid soybean amino ether Oils and Fats ester Co., Ltd.) 17polyoxyethylene polyoxyethylene D-230 N (Takemoto fatty acid castor oilether Oils and Fats Co., ester Ltd.) 18 polyoxyethylene polyoxyethylenerape D-233 N (Takemoto fatty acid seed oil ether Oils and Fats Co.,ester Ltd.) 19 polyoxyethylene polyoxyethylene oleyl Noigen ET-120Efatty acid ether (Daiichi Kogyo ester Seiyaku Co., Ltd.) 20polyoxyethylene polyoxyethylene fatty Spray Sticker (Nihon fatty acidacid ester (70%) Nohyaku Co., Ltd.) ester 21 silicone proprietary blend,of DyneAmic (Setre surface active polyalkylene oxide- Chemical) agentmodified polymethylsiloxane, nonionic emulsifiers, and methylatedvegetable oils 22 silicone proprietary blend of KINETIC (Setre surfaceactive polyalkylene oxide- Chemical) agent modified polydimethylsiloxaneand nonionic surface active agents 23 silicone (No. 23) silicone SILWETTL-77 surface active polyalkylene oxide (Witco) agent modifiedpolydimethyl siloxane 24 Silicone silicone polyalkylene SLIPPA(Interagro) surface active oxide modified Organosilicone agent (No. 23polydimethyl siloxane (Silwet L-77) and Linear and linear alcoholalcohol surfactant blend surfactant blend) 25 polyoxyethylene ethyleneoxide-adduct Lutensol FSA10 fatty acid of fatty acid amide (BASF AG)amide No. Designation Trade Name (Manufacturer) 26 octylphenoxy CitowettPLUS (BASF AG) or polyethoxyethanol CITOWETT PLUS 27 dilauryl esterpolyethylene COADJUVANT Chevron glycol ester solvent c.s.p. (Bayer AG)28 polioxiester amino grass 80 g, Hi-Point (CARGIL) solvente 29polyoxyethylene rosin ester Sorpol 7261 (Toho Chemical Industry Co.,Ltd.) 30 diglycerin diol fatty acid Sorpol 7337 (Toho Chemical ester +polyoxyethylene Industry Co., Ltd.) monomethyl ether 31 polyoxyethylenerosin ester Sorpol 7445 (Toho Chemical Industry Co., Ltd.) 32trimethylnonyl Surfactant WK polyethoxyethanol 33 polyglycol alkylarylether TREND ® (E.I. du Pont) 34 ethylene-acrylic acid Poligen WE3 (BASFAG) copolymer emulsion 35 Pepol AH-053 Lot. No. 2184Y (Toho ChemicalIndustry Co., Ltd.) 36 benceno Surfonato de sodio COADJUVANT TRITONACT-M eter 45 37 Aceitte Mineral 85% COADJUVANT ACETITE ANPLUS 38Aceitte Mineral 83% COADJUVANT ASSIST OIL 39 linear alcohol ethoxylate 7Ethylan D257 mols EO

Suitable anionic surface active agents which can be used asactivity-enhancing ingredient (c) include sulfuric ester surface activeagents, such as alkylsulfuric esters or salts thereof; sulfonic acidsurface active agents, such as naphthylmethanesulfonates and ligninsulfonates; fatty acid salts; and fluorine-containing surface activeagents, with sulfuric ester and sulfonic acid surface active agentsbeing preferred. Examples of preferred anionic surface active agents areshown in Table 2 below. TABLE 2 Nonionic Surface Active Agents TradeName No. Kind Designation (Manufacturer) 40 higher alcohol sodium higheralcohol Monogen sulfuric acid sulfate Y-100 ® ester (Daiichi KogyoSeiyaku Co., Ltd.) 41 dialkylsulfosuccinate sodium New Kalgendialkylsulfosuccinate EP-70G (Takemoto Oils & Fats Co., Ltd.) 42 ″sodium di-2- Genopur SB ethylhexyl- 1970J sulfosuccinate (Hoechst AG) 43sodium Hostapon T Pow. oleylmethyltauride H/C (Hoechst AG) 44 alkyldiglycol ether Genapol LRO sulfate salt based on paste natural fatty(Hoechst AG) alcohols; RO—(EO)₂—SO₃Na 45 linosulfa to de COADJUVANTcalcio 20 + 12 RINO

Suitable cationic surface active agents which can be used asactivity-enhancing ingredient (c) include dialkylammonium salts such asNEEDS (a trade mark, produced by Kao Corporation); and alkylammoniumsalts such as Arguard T/50 (trade name, produced by Akzo Chemical) asshown in Table 3 below. TABLE 3 Cationic Surface Active Agents TradeName No. Kind Designation (Manufacturer) 46 dialkylammoniumpolynaphthyl- NEEDS (Kao salt methanesulfonate Corporation) dialkyldimethyl- ammonium polyoxyethylene fatty acid ester 47 polyoxyethyleneRHODAMEEN ® aliphatic amine (RHÔNE-POULENC)

The animal and/or vegetable oil which can be used as activity-enhancingingredient (c) include vegetable oil, such as corn oil, soybean oil,linseed oil, sunflower oil, cotton seed oil, and rape seed oil; andanimal oil, such as beef tallow and train oil (whale oil). Alkylated(e.g., methylated) vegetable oil such as SCOIL (manufactured by MVRC) isalso included. Specific examples of suitable animal and/or vegetable oilare shown in Table 4 below. Among these, alkylated vegetable oil ispreferred. TABLE 4 Animal and/or Vegetable Oil No. Kind No. Kind(Manufacturer) 48 corn oil 53 soybean 90% emulsion 49 corn oil emulsion54 soybean oil 50 corn oil emulsion 55 SCOIL (MVRC) 51 corn oil emulsion56 linseed oil emulsion (ICI Agrochemicals) 52 soybean oil 57 animal oilEthokem (Midkem Agrochemicals) No. Kind Designation Trade Name 58coconut modified coco Seawet or SEAWET oil diethanolamide/inert(Sea-Born ingredients couplers Subsidiary and solubilizing agents Lane,Inc.)

The paraffin oil which can be used as activity-enhancing ingredient (c)includes product originated animal and/or vegetable oil, productoriginated mineral oil (e.g., petroleum), and mixtures thereof. Specificexamples are shown in Table 5 below. TABLE 5 Paraffin Oil Trade name No.Kind Designation (Manufacturer) 59 paraffin oil ATPLUS 411F (ICIAgrochemicals 60 ″ ATPLUS 411F OIL (ICI Agrochemicals) 61 ″ nonionic SUNOIL ADJUVANT surfactant (Schering Agrochemicals, Ltd.) 62 ″ petroleumbased OLEOTAN (Biomex) paraffinic oil nonionic surfactants 63 ″petroleum based PRIME OIL paraffinic oil nonionic surfactants

The mineral oil which can be used as activity-enhancing ingredient (c)include machine oil, fuel oil, and silicone oil. Examples of preferredmineral oil are shown in Table 6 below. Among these, ISHIOIL(manufactured by Ishihara Sangyo Kaisha, Ltd.) is the most preferred.TABLE 6 Mineral Oil Trade Name No. Kind Designation (Manufacturer) 64mineral oil machine oil (machine oil) emulsion 65 mineral oil machineoil (machine oil) emulsion (Toho Chemical Industry Co., Ltd.) 66 mineraldiesel engine oil oil (fuel emulsion oil) 67 mineral oil mineral oil(98%) + tensio ISHIOIL (Ishihara activo Sangyo Kaisha, (2%) Ltd.) 68 ″blend of heavy AGRI-DEX or Agri- range paraffin Dex (Helena basepetroleum Chemical Company) oil, polyol fatty acid esters, andpolyethoxylated derivatives

The above-described spreaders, i.e., surface active agents (exceptsorbitan higher fatty acid esters), animal and/or vegetable oil,paraffin oil, mineral oil, etc.) can be combined appropriately for useas activity-enhancing ingredient (c). Combinations of two or morespreaders include vegetable oil containing surface active agents, suchas Soy Dex (Helena Chemical Company) etc.; and paraffin oil containingsurface active agents, such as Oleo DP 11E (E.I. du Pont), Fyzol 11E(Schering Agrochemicals), Agri Dex (Helena Chemical Co.), Atplas 411(ICI Agrochemicals), HerbiLmax (Love Land Industries, Inc.), CompetitorCrop. Oil Concentrate (Red Pancer Chemical), Actipron (Oil Co.), DASH(BASF AG), Atlas Adherb (Atlas Interlates, Ltd.), Cropspray (TribartFarm Chemical), Agravia 11E (Wakker Chemie), Penetrator (Helena ChemicalCo.), Atlus Adjuvant Oil (Atlus Interlates, Ltd.), etc. Mixed spreadersshown in Table 7 are also included. TABLE 7 Mixed Spreaders No.Designation Trade Name 69 mineral oil + vegetable mineral oil emulsion +soybean oil oil emulsion 70 2-pyrrolidione + 1- Agrimax 3Hoctyl-2-pyrrolidione + 1- ethenyl-1-hexadecyl homopolymer + calciumdodecylbenzenesulfonate

As stated above, any spreader can be used in the present invention asfar as it significantly enhances the physical properties of theimidazole compound of formula (I) to enhance the effects of thecompound, whatever kind it belongs to. Specific examples of usefulspreaders that cannot be classified into any of the above listed kindsare shown in Table 8 below. As a matter course, a composition forcontrolling harmful bio-organisms containing at least one imidazolecompound of formula (I) as active ingredient (a) having incorporatedtherein the spreader usable as activity-enhancing ingredient (c) in aratio according to the present invention is expected to exhibit similareffects. TABLE 8 Unclassifiable Spreaders No. Designation Trade Name(Manufacturer) 71 Adherex MR (ISK Mexico) 72 Atlox-BI (Kao Corporation)73 sol de olamina del acido EXTRAVON ® 40 (Ciba-Geigy dodecil bencenoAgrochemicals, Ltd.) sulfuronico (33%) + solvente (aqua) estabilizante eimpurezas (67%) 74 SUPER CORAL ADH-50 (Grupocoret) 75 SURFATE 30 (E.I.du pont) 76 ALBOL INEUM AK (ICI Agrochemicals) 77 ATPLUS SL 92 (ICIAgrochemicals) 78 Nisseki Noyaku Oil Emulsion (Nippon Oil Co., Ltd.) 79OLEO RUSTICA 11E (Hoechst AG) 80 SURF OIL (Hoechst AG) 81 ADJUVANT No. 1(Toho Chemical Industry Co., Ltd.) 82 aceitte parafinico 81% Ulvapron ®83 X2-5309 (Toray Industries, Inc.) 84 blend of alkylphenyl HelenaSurfix (Helena hydroxy-polyoxyethylene Chemical Co.) polymerized resinsand fatty acids (78%) + paraffin base petroleum oil (22%) 85 HelenaSuraid (Helena Chemical Co.) 86 COADJUVANT NATURL OIL (Stoller ChemicalCo.) 87 polioxy ester amino graso COADJUVANT SP-SUPER 42 88 syntheticlatex (45%) + primary Bond (Loveland aliphatic Industries, Inc.)oxyalkylated alcohol (10%) + inert ingredients (45%) 89 higher alkylpyrrolidones Banka (formerly ANKA) combined with water- (Interagro)insoluble polymers (pseudo cationic polymers) and surfactants 90alkoxylated amine ARMA (Interagro) (alkoxylated fatty aminepolymer)/polysaccharide (sugar-based nonionic surfactant and buffer)blend 91 modified LATRON B-1956 (Rohm & phthalic/glycerol alkyl HaasCo.) resin (77%) + butyl alcohol (23%) 92 blend of DL-1-p-mentheneLASTIC (Helena Chemical (96%) + inert ingredients Co.) (4%)

The above-described fungicides for Phycomycetes as active ingredient (b)characteristically have one or more of a preventive effect, a curativeeffect and penetrability. Some of the inorganic phosphorus compounds asactive ingredient (b), which are not fungicides, possess one or more ofa preventive effect, a curative effect, and penetrability similarly tothe fungicides for Phycomycetes.

The term “fungicides having a preventive effect” means that thefungicides have an ability of preventing plant diseases. Examples ofsuch fungicides include β-methoxyacrylate compounds, oxazolidinedionecompounds, cyanoacetamide compounds, organic chlorine compounds,phenylamide compounds, cinnamic acid compounds, copper compounds, andorganophosphorus compounds.

The term “fungicides having a curative effect” means that the fungicidescan migrate through the plant body to control an invading harmfulbio-organism. Examples of such fungicides include β-methoxyacrylatecompounds, cyanoacetamide compounds, phenylamide compounds, cinnamicacid compounds, and organophosphorus compounds.

The term “fungicides having penetrability” means that the fungicideshaving an ability of penetrating through the surface of leaves into theinside. Examples of such fungicides include β-methoxyacrylate compounds,oxazolidinedione compounds, cyanoacetamide compounds, phenylamidecompounds, cinnamic acid compounds, and organophosphorus compounds.

In addition to the fungicides that have been named, other fungicides forPhycomycetes having at least one of a preventive effect, a curativeeffect and penetrability are also expected to produce the same effectsas observed in the present invention. For example, dithiocarbamatefungicides can be mentioned as an example of fungicides for Phycomyceteshaving only a preventive effect.

The compositions for controlling harmful bio-organisms according to thepresent invention which comprises at least one imidazole compound offormula (I) as active ingredient (a) and at least one inorganicphosphorus compound as active ingredient (b) are particularly suitablefor agricultural and horticultural uses. Specifically, they exhibitexcellent effects of controlling diseases of crop plants, such as riceblast caused by Pyricularia oryzae, rice sheath blight caused byRhizoctonia solani, cucumber anthracnose caused by Colletotrichumlagenarium, cucumber powdery mildew caused by Sphaerotheca fuliginea,cucumber downy mildew caused by Pseudoperonospora cubensis, tomato lateblight caused by Phytophthora infestans, tomato early blight caused byAlternaria solani, citrus melanose caused by Diaporthe citri, citruscommon green mold caused by Penicillium digitatum, pear scab caused byVenturia nashicola, apple Alternaria blotch caused by Alternaria mali,grape downy mildew caused by Plasmopara viticola, gray mold caused byBotrytis cinerea, Sclerotial rot caused by Sclerotinia sclerotiorum, anddisease caused by rust, etc.; and soil diseases caused byphytopathogenic fungi, such as Fusarium, Pythium, Rhizoctonia,Verticillium, and Plasmodiophora, etc. In particular, the compositionsof the present invention exhibit excellent effects of controllingdiseases such as potato late blight caused by Phytophthora infestans,sweet pepper Phytophtora blight caused by Phytophthora capsici,watermelon Phytophthora rot caused by Phytophthora drechsleri, tobaccoblack shank caused by Phytophthora nicotianae var. nicotianae, tomatolate blight caused by Phytophthora infestans, cucumber or melon downymilder caused by Pseudoperonospora cubensis, cabbages or Chinesecabbages downy mildew caused by Peronospora brassicae, onion downymildew caused by Peronospora destructor, onion shiroiro-eki-byo causedby Phytophthora porri and watermelon brown rot caused by Phytophthoracapsici, and grapedowny mildew caused by Plasmopara viticola and varioussoil diseases caused by e.g., Aphanomyces, Pythium. The compositionshave a prolonged residual effect and exhibit a particularly excellentcurative effect. It is therefore possible to control diseases bytreatment after infection. In addition, since the compositions possess asystemic activity, it is possible to control diseases of stems andfoliage by soil treatment.

The compositions for controlling harmful bio-organisms according to thepresent invention which comprises at least one imidazole compound offormula (I) as active ingredient (a) and a fungicide for Phycomycetes asactive ingredient (b) have excellent bactericidal activities whenapplied to crop plants, for example, fruit vegetables (e.g., cucumbers,tomatoes, eggplants, etc.); cereals (e.g., rice, wheat, etc.); seedvegetables; fruits (e.g., apples, pears, grapes, citrus, etc.);potatoes, etc., which have been infected, or suspected of beinginfected, with pathogenic fungi. They exhibit excellent controllingeffects on diseases, such as powdery mildew, downy mildew, anthracnose,gray mold, common green mold, Sclerotial rot, scab, Alternaria blotch,bacterial spot, black spot, melanose, ripe rot, late blight, earlyblight, blast, sheath blight, damping-off, southern blight, etc. Thecompositions also exert excellent controlling effects on soil diseasescaused by Phycomycetes, such as Pythium, and other plant pathogens, suchas Fusarium, Rhizoctonia, Verticillium, Plasmodiophora, etc. Thecompositions have a prolonged residual effect and exhibit a particularlyexcellent curative effect. It is therefore possible to control diseasesby treatment after infection. In addition, since the compositionspossess a systemic activity, it is possible to control diseases of stemsand foliage by soil treatment.

In particular, the compositions comprising at least one imidazolecompound of formula (I) as active ingredient (a) and a copper compoundand/or an organophosphorus compound as a fungicide for Phycomycetes asactive ingredient (b) are particularly useful in agriculture andhorticulture. Specifically, the compositions exhibit excellent effectsof controlling diseases of crop plants, such as rice blast caused byPyricularia oryzae, rice sheath blight caused by Rhizoctonia solani,cucumber anthracnose caused by Colletotrichum lagenarium, cucumberpowdery mildew caused by Sphaerotheca fuliginea, cucumber downy mildewcaused by Pseudoperonospora cubensis, tomato late blight caused byPhytophthora infestans, tomato early blight caused by Alternaria solani,citrus melanose caused by Diaporthe citri, citrus common green moldcaused by Penicillium digitatum, pear scab caused by Venturia nashicola,apple Alternaria blotch caused by Alternaria mali, grape downy mildewcaused by Plasmopara viticola, gray mold caused by Botrytis cinerea,sclerotinia rot caused by Sclerotinia sclerotiorum, rust, bacterialspot, etc.; and soil diseases caused by phytopathogenic fungi, such asFusarium, Pythium, Rhizoctonia, Verticillium, Plasmodiophora, etc. Inparticular, the compositions of the present invention exhibit excellenteffects of controlling diseases such as potato or tomato late blightcaused by Phytophthora infestans, cucumber downy mildew caused byPseudoperonospora cubensis, grape downy milder caused by Plasmoparaviticola; and various soil diseases caused by Phycomycetes, such asPlasmodiophora, Aphanomyces, Pythium, etc.

The compositions of the present invention have a prolonged residualeffect so that they exhibit an excellent preventive effect, and alsoexhibit an excellent curative effect as well. It is therefore possibleto control diseases by treatment after infection. In addition, sincethey possess a systemic activity, it is also possible to controldiseases of the stem and leaf by soil treatment.

In particular, the compositions containing a copper compound as afungicide for Phycomycetes exhibit an excellent preventive effect, andthe compositions containing an organophosphorus compound as a fungicidefor Phycomycetes exhibit an excellent curative effect.

The compositions for controlling harmful bio-organisms comprising atleast one imidazole compound of formula (I) as active ingredient (a) anda cyanoacetamide compound, a phenylamide compound or a cinnamic acidcompound as a fungicide for Phycomycetes as active ingredient (b)exhibit excellent controlling effects on diseases caused byPhycomycetes, such as plant diseases, e.g., downy mildew of cucumbers,melons, cabbages, Chinese cabbages, onions, pumpkins, and grapes; lateblight of potatoes, red peppers, sweet peppers, watermelons, pumpkins,tobaccos, and tomatoes; onion shiroiro-eki-byo; watermelon brown rot;soil diseases caused by plant pathogenic fungi, such as Pythium, etc. Italso has excellent controlling effects on diseases caused byPlasmodiophora.

The compositions for controlling harmful bio-organisms comprising atleast one imidazole compound of formula (I) as active ingredient (a) anda β-methoxyacrylate compound, an oxazolidinedione compound or an organicchlorine compound as a fungicide for Phycomycetes as active ingredient(b) exhibit excellent controlling effects against diseases caused byPhycomycetes, such as plant diseases, e.g., rice blast; rice sheathblight; cucumber anthracnose; downy mildew of cucumbers, melons,cabbages, Chinese cabbages, onions, pumpkins, and grapes; powdery mildewof wheat, barley and cucumbers; late blight of potatoes, red peppers,sweet peppers, watermelons, pumpkins, tobaccos, and tomatoes; wheatspeckled leaf blotch; tomato early blight; citrus melanose; citruscommon green mold; pear scab; apple Alternaria blotch; onionshiroiro-eki-byo; watermelon brown rot; various diseases such as graymold, sclerotial rot, rust, and bacterial spot; various soil diseasescaused by plant pathogenic fungi, etc., such as Fusarium, Pythium,Rhizoctonia, Verticillium, etc. It also has excellent controllingeffects on diseases caused by Plasmodiophora. The compositions showparticularly excellent controlling effects on diseases such asPhytophthora rot of potatoes, red peppers, sweet peppers, watermelons,pumpkins, tobaccos, tomatoes, etc.; and downy mildew of cucumbers,melons, cabbages, Chinese cabbages, onions, pumpkins, grapes, etc.

Further, the compositions comprising active ingredients (a) and (b) ofthe present invention show an excellent controlling effect againstagriculturally and horticulturally harmful insects, such as planthoppers(Delphacidae), diamondback moth (Plutella xylostella), green riceleafhopper (Nephotettix cincticeps), adzuki bean weevil (Callosobruchuschinensis), common cutworm (Spodoptera litura), green peach aphid (Myzuspersicae), etc.; mites, such as two-spotted spider mite (Tetranychusurticae), carmine spider mite (Tetranychus cinnabarinus), citrus redmite (Panonychus citri), etc.; and nematodes, such as southern root-knotnematode (Meloidogyne incognita), etc.

The compositions for controlling harmful bio-organisms comprising activeingredient (a) and activity-enhancing ingredient (c) of the presentinvention are particularly suitable for agricultural and horticulturaluses. The harmful bio-organisms which can be controlled by thecompositions include plant pathogenic fungi causing plant diseases, suchas rice blast; rice sheath blight; cucumber anthracnose; cucumberpowdery mildew; downy milder of cucumber, melon, cabbage, Chinesecabbage, onion and grape; late blight of potato, red pepper, sweetpepper, watermelon, pumpkin, tobacco; tomato Phytophthora rot; tomatoearly blight; citrus melanose; citrus common green mold; pear scab;apple Alternaria blotch; various plant diseases such as gray mold,sclerotial rot, rust, etc.; soil borne pathogenic fungi causing variousplant diseases, such as Fusarium, Pythium, Rhizoctonia, Verticillium,Plasmodiophora, etc.; insects, such as planthoppers, diamondback moth,green rice leafhopper, adzuki bean weevil, common cutworm, green peachaphid, etc.; mites, such as two-spotted spider mite, carmine spidermite, citrus red mite, etc.; and nematodes, such as southern root-knotnematode, etc. More specifically, they are effective on Phytophthora rotof potatoes, red peppers, sweet peppers, watermelons, pumpkins,tobaccos, and tomatoes and downy mildew of cucumbers, melons, cabbages,Chinese cabbages, onions, pumpkins, and grapes. The compositionscomprising active ingredient (a) and activity-enhancing ingredient (c)have a prolonged residual effect and exhibit not only an excellentpreventive effect but an excellent curative effect. It is thereforepossible to control diseases by treatment after infection.

The active ingredients, inclusive of other pesticides hereinafterdescribed as well as active ingredients (a) and (b), andactivity-enhancing ingredient (c) which constitute the compositions forcontrolling harmful bio-organisms of the present invention can beformulated into a variety of forms, such as emulsifiable concentrates,dusts, wettable powders, aqueous solutions, granules, suspensionconcentrates, etc., together with various adjuvants, as in conventionalagricultural preparations. Active ingredient (a) (the imidazole compoundof formula (I)), active ingredient (b) and other specific compounds maybe mixed and formulated, or each of them may be separately formulatedand then mixed together. Upon use, the preparation may be used as suchor as diluted with an appropriate diluent, e.g., water, to apredetermined concentration.

Examples of the adjuvants which can be used include carriers,emulsifying agents, suspending agents, thickeners, stabilizers;dispersants, spreaders except those used as activity-enhancingingredient (c), surface active agents, wetting agents, penetratingagents, antifreezing agents, antifoaming agents, etc. These adjuvantsare added appropriately according to necessity.

The carriers are classified into solid carriers and liquid carriers. Thesolid carriers include animal and vegetable powders (e.g., starch,sugar, cellulose powders, cyclodextrin, activated charcoal, soybeanpowders, wheat powders, chaff powders, wood powders, fish powders,powdery milk, etc.); and mineral powders (e.g., talc, kaolin, bentonite,bentonite-alkylamine complexes, calcium carbonate, calcium sulfate,sodium hydrogencarbonate, zeolite, diatomaceous earth, white carbon,clay, alumina, silica, sulfur powder, slaked lime, etc.). Examples ofthe liquid carriers include water, vegetable oils (e.g., soybean oil,cotton seed oil), animal oils (e.g., beef tallow, train oil, etc.),alcohols (e.g., ethyl alcohol, ethylene glycol, etc.), ketones (e.g.,acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, etc.),ethers (e.g., dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons(e.g., kerosene, lamp oil, liquid paraffin, etc.), aromatic hydrocarbons(e.g., toluene, xylene, trimethylbenzene, tetramethylbenzene,cyclohexane, solvent naphtha, etc.), halogenated hydrocarbons (e.g.,chloroform, chlorobenzene, etc.), acid amides (e.g., dimethylformamide,etc.), esters (e.g., ethyl acetate, fatty acid glycerine esters, etc.),nitriles (e.g., acetonitrile, etc.), sulfur-containing compounds (e.g.,dimethyl sulfoxide, etc.), N-methyl-2-pyrrolidone, N,N-dimethylformamideand so on. The spreaders (except those used as activity-enhancingingredient (c)) or surface active agents include polyoxyethylenesorbitan fatty acid esters.

In the compositions comprising at least one imidazole compound offormula (I) as active ingredient (a) and at least one inorganicphosphorus compound as active ingredient (b), the weight ratio of (a) to(b) is usually 1:300 to 300:1, preferably 1:100 to 100:1, stillpreferably 1:50 to 5:1, most preferably 1:50 to 1:10.

In the compositions comprising at least one imidazole compound offormula (I) as active ingredient (a) and at least one fungicide forPhycomycetes as active ingredient (b), the weight ratio of (a) to (b) isusually 1:10000 to 10000:1, preferably 1:1000 to 10000:1, stillpreferably 1:100 to 1000:1. Especially in the compositions containing atleast one imidazole compound of formula (I) as active ingredient (a) andat least one cyanoacetamide compound as active ingredient (b) (fungicidefor phycomycetes) is preferably 1:300 to 5:1. Where, in particular,copper compounds and/or organophosphorus compounds are used as activeingredient (b) (fungicide for Phycomycetes), the weight ratio of (a) to(b) is usually 1:2000 to 2000:1, preferably 1:300 to 300:1, stillpreferably 1:100 to 100:1, particularly preferably 1:50 to 5:1.

In the compositions containing active ingredient (a) andactivity-enhancing ingredient (c), the weight ratio of (a) to (c) isusually 1:5000 to 2000:1, preferably 0.05:99.95 to 90:10, stillpreferably 0.2:99.8 to 80:20.

A method for controlling harmful bio-organisms comprising applying thecompositions for controlling harmful bio-organisms of the preventinvention is also included under the scope of the present invention.

In using the compositions for controlling harmful bio-organismscomprising at least one imidazole compound of formula (I) as activeingredient (a) and at least one inorganic phosphorus compound as activeingredient (b), the concentrations of use of the active ingredients (a)and (b) cannot be generally defined because they vary depending on, forexample, the crop plant to be treated, the method of treatment, the formof the preparation, and the amount of the preparation to be applied. Forexample, the imidazole compound of formula (I) and the inorganicphosphorus compound are used in concentrations of 1 to 1000 ppm and 1 to5000 ppm, respectively, in foliar treatment, and 10 to 10,000 g/ha and10 to 50,000 g/ha, respectively, in soil treatment.

In using the compositions for controlling harmful bio-organismscomprising at least one imidazole compound of formula (I) as activeingredient (a) and at least one fungicide for Phycomycetes selected fromthe group consisting of a β-methoxyacrylate compound, anoxazolidinedione compound, a cyanoacetamide compound, an organicchlorine compound, a phenylamide compound, and a cinnamic acid compoundas active ingredient (b), the concentrations of use of the activeingredients cannot be generally defined because they vary depending onthe kind of the fungicide used, the crop plant to be treated, the methodof treatment, the form of the preparation, the amount of the preparationto be applied, the timing of treatment, and the kind of the harmfulfungi to be controlled. For foliar treatment, for example, the imidazolecompound of formula (I) and the fungicide are used in concentrations of0.01 to 1000 ppm and 0.01 to 1000 ppm, respectively, preferably 0.1 to500 ppm and 0.1 to 500 ppm, respectively.

In using the compositions for controlling harmful bio-organismscomprising at least one imidazole compound of formula (I) as activeingredient (a) and a copper compound and/or an organophosphorus compoundas active ingredient (b), the concentrations of use of the activeingredients cannot be generally defined because they vary depending on,for example, the kind of the fungicide used, the crop plant to betreated, the method of treatment, the form of the preparation, theamount of the preparation to be applied, the timing of treatment, andthe kind of the harmful fungi to be controlled. For example, theimidazole compound of formula (I) and the fungicide are used inconcentrations of 0.01 to 1000 ppm and 1 to 5000 ppm, respectively, infoliar treatment and 10 to 10,000 g/ha and 10 to 50,000 g/ha,respectively, in soil treatment.

In using the compositions comprising active ingredient (a) andactivity-enhancing ingredient (c), the concentrations of use of theseingredients cannot be generally defined because they vary depending on,for example, the crop plant to be treated, the method of treatment, theform of the preparation, and the amount of the preparation to beapplied. For example, active ingredient (a) and activity-enhancingingredient (c) are used in concentrations of 0.1 to 10,000 ppm and 0.01to 50 ppm, respectively, in foliar treatment and 0.01 to 100 kg/ha and0.1 to 0-0.5 kg/ha, respectively, in soil treatment.

The compositions comprising active ingredients (a) and (b) can be usedas a mixture or in combination with, for example, other pesticides,fertilizers, and safeners, to exhibit enhanced effects and actions.Useful pesticides include bactericides except those used as activeingredients (a) and (b), fungicides, insecticides, acaricides,nematicides, antiviral agents, attaractants, herbicides, and plantgrowth regulators. In particular, mixtures or combinations of thecompositions for controlling harmful bio-organisms of the presentinvention and one or more active ingredients of fungicides other thanthose used as active ingredients (a) and (b) can enjoy enhancements, forexample, in terms of the range of controllable harmful bio-organisms,the timing of treatment, and the controlling activity on harmfulbio-organisms. The imidazole compound of formula (I) as activeingredient (a), the inorganic phosphorus compound and/or fungicide forPhycomycetes as active ingredient (b), and the active ingredient(s) offungicides other than those used as active ingredients (a) and (b) canbe separately formulated and mixed together on use, or one or at leasttwo of them can be mixed and formulated into a single preparation.

Where at least one imidazole compound of formula (I) as activeingredient (a) is combined with at least one of the inorganic phosphoruscompound and/or at least one of the fungicides for phycomycetes asactive ingredient (b), a composition prepared immediately before usemanifests further enhanced controlling effects over a previouslyprepared composition. Therefore, it is convenient that a compositioncontaining active ingredient (a) and, if desired, various adjuvants anda composition containing active ingredient (b) and, if desired, variousadjuvants are separately packed and supplied as a two-pack preparation.For example, active ingredient (a) and active ingredient (b) can bedissolved in respective liquid carriers and packed separately, or activeingredient (a) and a mixture of active ingredient (b) and otherfungicides are dissolved in respective liquid carriers and packedseparately.

In the harmful bio-organism controlling method using the compositionscomprising active ingredient (a) and activity-enhancing ingredient (c),the compositions can be used as a mixture with the above-described otherpesticides, which can bring about further enhanced effects. Typicalexamples of useful other pesticides include azole compounds such asTriflumizole (common name), etc.; quinoxaline compounds such asQuinomethionate (common name), etc.; benzimidazole compounds such asBenomyl (common name), etc.; pyridinamine compounds such as Fluazinam(common name), etc.; sulfenic acid compounds such as Dichlofluanid(common name), etc.; isoxazole compounds such as Hydroxyisoxazole(common name), etc.; dicarboxyimide compounds such as Procymidone(common name), etc.; benzanilide compounds such as Flutolanil (commonname) etc.; and benzamide compounds such as(R,S)-4-chloro-N-[cyano(ethoxymethyl]benzamide, etc.

Preferred embodiments of the compositions for controlling harmfulbio-organisms according to the present invention which comprise activeingredients (a) and (b) are shown below for illustrative purposes onlybut not for limitation.

(1) The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have a preventive effect.

(2) The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have a curative effect.

(3) The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have penetrability.

(4) The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have a preventive effect and a curative effect.

(5) The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have a preventive effect and penetrability.

(6). The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have a curative effect and penetrability.

(7) The compositions for controlling harmful bio-organisms wherein atleast one inorganic phosphorus compound and/or at least one fungicidefor Phycomycetes have a preventive effect, a curative effect andpenetrability.

(8) The compositions for controlling harmful bio-organisms whereinactive ingredient (b) is at least one inorganic phosphorus compound.

(9) The compositions for controlling harmful bio-organisms whereinactive ingredient (b) is at least one fungicide for Phycomycetes.

(10) The compositions for controlling harmful bio-organisms according to(9) above, wherein the fungicide for Phycomycetes is a compound selectedfrom the group consisting of a β-methoxyacrylate compound, anoxazolidinedione compound, a cyanoacetamide compound, an organicchlorine compound, a phenylamide compound, a cinnamic acid compound, acopper compound, and an organophosphorus compound.

(11) The compositions for controlling harmful bio-organisms according to(9) above, wherein the fungicide for Phycomycetes is a β-methoxyacrylatecompound and/or an oxazolidinedione compound.

(12) The compositions for controlling harmful bio-organisms according to(9) above, wherein the fungicide for Phycomycetes is a compound selectedfrom the group consisting of a cyanoacetamide compound, an organicchlorine compound, a phenylamide compound, a cinnamic acid compound, acopper compound, and an organophosphorus compound.

(13) The compositions for controlling harmful bio-organisms according to(9), (10) or (11) above, wherein the fungicide for Phycomycetes is aβ-methoxyacrylate compound.

(14) The compositions for controlling harmful bio-organisms according to(13), wherein the β-methoxyacrylate compound is methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylateor methyl (E)-methoxyimino[α-(o-tolyloxy)-O-tolyl]acetate.

(15) The compositions for controlling harmful bio-organisms according to(9), (10) or (11), wherein the fungicide for Phycomycetes is anoxazolidinedione compound.

(16) The compositions for controlling harmful bio-organisms according to(15), wherein the fungicide for Phycomycetes is3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione.

(17) The compositions for controlling harmful bio-organisms according to(9), (10) or (12), wherein the fungicide for Phycomycetes is acyanoacetamide compound.

(18) The compositions for controlling harmful bio-organisms according to(17), wherein the cyanoacetamide compound is1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea.

(19) The compositions for controlling harmful bio-organisms according to(9), (i) or (12), wherein the fungicide for Phycomycetes is an organicchlorine compound.

(20) The compositions for controlling harmful bio-organisms according to(19), wherein the organic chlorine compound istetrachloroisophthalonitrile or pentachloronitrobenzene.

(21) The compositions for controlling harmful bio-organisms according to(19), wherein the organic chlorine compound istetrachloroisophthalonitrile.

(22) The compositions for controlling harmful bio-organisms according to(9), (10) or (12), wherein the fungicide for Phycomycetes is aphenylamide compound.

(23) The compositions for controlling harmful bio-organisms according to(22), wherein the phenylamide compound is at least one compound selectedfrom the group consisting of methylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate,2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)aceto-2′,6′-xylidide,(±)-α-2-chloro-N-(2,6-xylylacetamide)-γ-butyrolactone, methylN-phenylacetyl-N-(2,6-xylyl)-DL-alaninate, methylN-(2-furoyl)-N-(2,6-xylyl)-DL-alaninate, and(±)-α-[N-(3-chlorophenyl)-cyclopropanecarboxamide]-γ-butyrolactone.

(24) The compositions for controlling harmful bio-organisms according to(22), wherein the phenylamide compound is methylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate.

(25) The compositions for controlling harmful bio-organisms according to(9), (10) or (12), wherein the fungicide for Phycomycetes is a cinnamicacid compound.

(26) The compositions for controlling harmful bio-organisms according to(25), wherein the cinnamic acid compound is(E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine.

(27) The compositions for controlling harmful bio-organisms according to(9), (10) or (12), wherein the fungicide for Phycomycetes is a coppercompound and/or an organophosphorus compound.

(28) The compositions for controlling harmful bio-organisms according to(27), wherein the copper compound is an inorganic copper fungicideand/or an organic copper fungicide.

(29) The compositions for controlling harmful bio-organisms according to(28), wherein the active ingredient of the inorganic copper fungicide isat least one member selected from the group consisting of cuprichydroxide, copper oxysulfate, copper oxychloride, anhydrous copper (II)sulfate, and basic copper calcium sulfate.

(30) The compositions for controlling harmful bio-organisms according to(27), wherein the organophosphorus compound is at least one memberselected from the group consisting of aluminum tris(ethyl phosphonate),O-2,6-dichloro-p-tolyl-O,O-dimethyl phosphorothioate,(R,S)-S-(R,S)-sec-butyl-β-ethyl-2-oxo-2-thiazolidinyl phosphonothioate,S-benzyl diisopropyl phosphorothioate, O-ethyl diphenylphosphorodithioate, and ethyl2-diethoxythiophosphoryloxy-5-methylpyrazolo(1,5-a)pyrimidine-6-carboxylate.

(31) The compositions for controlling harmful bio-organisms according to(27), wherein the organophosphorus compound is aluminum tris(ethylphosphonate).

(32) The compositions for controlling harmful bio-organisms according to(27), wherein the weight ratio of at least one imidazole compound offormula (I) to the copper compound and/or the organophosphorus compoundis 1:2000 to 2000:1.

Preferred embodiments of applying the composition containing activeingredient (a) and activity-enhancing ingredient (c) to harmfulbio-organisms are described below for illustrative purposes only but notfor limitation.

(1) The compositions containing active ingredient (a) andactivity-enhancing ingredient (c) can be applied to harmfulbio-organisms in the form of an aqueous dispersion. In this method, theaqueous dispersion is sprayed over the sites where a harmfulbio-organism has occurred or is expected to occur, such as foliage ofuseful plants or soil. The aqueous dispersion is particularly effectivefor application to foliage. The aqueous dispersion is prepared, forexample, by (i) dispersing a preparation of the active ingredient inwater and adding thereto the activity-enhancing ingredient; (ii)dispersing a preparation containing the active ingredient and theactivity-enhancing ingredient in water; or the method similar to (i) or(ii). The aqueous dispersion to be applied is prepared by using 1 literof water per 0.1 to 10,000 mg of the compositions for controllingharmful bio-organisms so as to have the active ingredient in aconcentration of 0.1 to 10,000 ppm. The aqueous dispersion is sprayed inan amount of 100 to 10,000 l/ha.

(2) The compositions containing active ingredient (a) andactivity-enhancing ingredient (c) can be applied in the form of anaqueous suspension in the same manner as for the aqueous dispersion. Theconcentration of the active ingredient in the aqueous suspension is 0.1to 10,000 ppm. The aqueous suspension is sprayed in an amount of 100 to10,000 l/ha.

Test Examples of the compositions for controlling harmful bio-organismsof the present invention in usage as an agricultural or horticulturalfungicide are given below for illustrative purposes.

TEST EXAMPLE 1 Test of Curative Effect on Cucumber Downy Mildew

A composition for controlling harmful bio-organisms containing CompoundNo. 1 and the inorganic phosphorus compound shown in Table 9 below in aconcentration of 100 ppm and 2000 ppm, respectively, was prepared bymixing an aqueous suspension concentrate of Compound No. 1 and a 20%wettable powder of the inorganic phosphorus compound. The 20% wettablepowder of the inorganic phosphorus compound was prepared in accordancewith Reference Formulation Example hereinafter given.

A cucumber (cultivars: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis). After 24 hours, 10 ml/pot of theabove-prepared composition was sprayed onto the plant by means of aspray gun. For comparison, the same test was carried out by using 10 mlof a composition containing 2000 ppm of the inorganic phosphoruscompound and containing no Compound No. 1 or 10 ml of a compositioncontaining 100 ppm of Compound No. 1 and containing no inorganicphosphorus compound. The plant was kept in a chamber set at 22 to 24° C.for 6 days, and the lesion area of the first leaf was measured, fromwhich the disease incidence rate (%) was calculated according to thefollowing formula. The results obtained are shown in Table 9.Incidence rate (%)=(a/b)×100wherein a is a lesion area of a treated plant; and b is a lesion area ofa control (non-treated plant).

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Table 9.Theoretical incidence rate (%)=(X ¹ ×Y ¹)/100

wherein X¹ is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y¹ is an incidence rate (%) of a plant treated withonly the inorganic phosphorus compound. TABLE 9 Curative Effect onCucumber Downy Mildew (Incidence Rate; %) Inorganic Phosphorus CompoundNo. 1 Compound, 2000 ppm 100 ppm 0 ppm Na₃PO₄.12H₂O 0 (90.2) 95Al(H₂PO₄)₃ 5 (95) 100  H₂(PO₃H) 12.5 (71.3) 75 Na₂HPO₃.5H₂O 0 (85.5) 90K₂HPO₄ 2.5 (90.2) 95 Na₂HPO₄ 2.5 (95) 100  none 95 100  (control)

TEST EXAMPLE 2 Test of Curative Effect on Cucumber Downy Mildew

A composition for controlling harmful bio-organisms containing CompoundNo. 1 in a prescribed concentration and the inorganic phosphoruscompound shown in Table 10 below in a concentration of 250 ppm wasprepared by mixing an aqueous suspension concentrate of Compound No. 1and a 20% wettable powder of the inorganic phosphorus compound. The 20%wettable powder of the inorganic phosphorus compound was prepared inaccordance with Reference Formulation Example hereinafter given.

A cucumber (cultivars: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis). After 24 hours, 10 ml/pot of theabove-prepared composition was sprayed onto the plant by means of aspray gun. For comparison, the same test was carried out by using 10ml/pot of a composition containing 250 ppm of the inorganic phosphoruscompound and containing no Compound No. 1 or 10 ml/pot of a compositioncontaining Compound No. 1 at a prescribed concentration and containingno inorganic phosphorus compound. The plant was kept in a chamber set at22 to 24° C. for 4 days, and the lesion area of the first leaf wasmeasured, from which the disease incidence rate (%) was calculatedaccording to the following formula. The results obtained are shown inTable 10.Incidence rate (%)=(a/b)×100wherein a is a lesion area of a treated plant; and b is a lesion area ofa control (non-treated plant).

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Table 10.Theoretical incidence rate (%)=(X ² ×Y ²)/100

wherein X² is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y² is an incidence rate (%) of a plant treated withonly the inorganic phosphorus compound. TABLE 10 Curative Effect onCucumber Downy Mildew (Incidence Rate; %) Inorganic Phosphorus CompoundNo. 1 Compound, 250 ppm 50 ppm 12.5 ppm 0 ppm Na₃PO₄.12H₂O 0 (77) 3 (81)90 Al(H₂PO₄)₃ 0 (85) 0 (90) 100  H₂(PO₃H) 0 (64) 3 (68) 75 Na₂HPO₃.5H₂O0 (72) 3 (77) 85 K₂HPO₄ 0 (81) 5 (86) 95 Na₂HPO₄ 3 (85) 3 (90) 100  none85 90 100  (control)

TEST EXAMPLE 3 Field Test of Effect on Cucumber Downy Mildew

Five cucumber seedlings (cultivars: Tokiwa Kohai Hikari No. 3, P type)in the two-leaf stage were planted in a divided area (3 m² each) of thefield located in Kusatsu City, Shiga, Japan on May 10, 1997. Acomposition containing 50 ppm of Compound No. 1 and 1500 ppm of aninorganic phosphorus compound shown in Table 11 below was sprayed in anamount of 500 ml per area by means of a small-sized spraying machine onJune 10 and 17. For comparison, the same field test was carried out byusing a composition containing only 1500 ppm of the inorganic phosphoruscompound or a composition containing only 50 ppm of Compound No. 1. OnJune 23, all the leaves were observed to obtain a control index inaccordance with the following rating system. The results obtained areshown in Table 11. Artificial infection with a pathogenic fungus was notconducted so that the disease was spontaneous. Control Index Severity ofDisease 5 The lesion area or length is less than 3% of that of a control(non-treated area). 4 The lesion area or length is 3% or more and lessthan 5% of that of the control. 3 The lesion area or length is 5% ormore and less than 10% of that of the control. 2 The lesion area orlength is 10% or more and less than 30% of that of the control. 1 Thelesion area or length is 30% or more of that of the control.

TABLE 11 Field Test on Cucumber Downy Mildew (Control Index) InorganicPhosphorus Compound No. 1 Compound, 1500 ppm 50 ppm 0 ppm Alexin 95 PS*5 1 Phytex 200 SL** 5 1 none 3 1Note:*An aqueous solution having an phosphorous acid concentration of 600g/l, available from Mass{overscore (o)}.**An aqueous solution having a phosphorous acid concentration of 200g/l, available from Horticura cc).

TEST EXAMPLE 4 Test of Curative Effect on Cucumber Downy Mildew

A cucumber (cultivars: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis). After 24 hours, 10 ml of a compositioncontaining the compounds shown in Tables 12 to 19 in respectiveconcentrations shown was sprayed onto the plant by means of a spray gun.The plant was kept in a chamber set at 22 to 24° C. for 6 days, and thelesion area of the first leaf was measured, from which the diseaseincidence rate (%) was calculated according to the following formula.The results obtained are shown in Tables 12 to 19.Incidence rate (%)=(a/b)×100wherein a is a lesion area of a treated plant; and b is a lesion area ofa control (non-treated plant).

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Tables 12 to19.Theoretical incidence rate (%) (X ³ ×Y ³)/100

wherein X³ is an incidence rate (%) of a plant treated with onlyCompound No. 1, 2 or 3; and Y³ is an incidence rate (%) of a planttreated with only compound (a) (i.e., methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate),compound (b) (i.e., methyl(E)-methoxyimino[α-(o-tolyloxy)-O-tolyl]acetate), Cymoxanil, Metalaxylor Dimethomorph. TABLE 12 Curative Effect on Cucumber Downy Mildew(Incidence Rate; %) Compound (a) Compound No. 1 63 ppm 2 ppm 0 ppm 500ppm 0 (0.5)  5 (10) 10 125 ppm 5  0 (5) 5  31 ppm 5  5 (50) 50  8 ppm 0(5)  5 (100) 100  0 ppm 5 100 (100) 100

TABLE 13 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Compound (b) Compound No. 1 500 ppm 125 ppm 0 ppm 500 ppm  10  0 (10) 10125 ppm  0 (5)  0 (5) 5  31 ppm  10 (50)  0 (50) 50  8 ppm  10 (100)  10(100) 100  0 ppm 100 100 100

TABLE 14 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Compound (a) Compound No. 3 2 ppm 0 ppm 125 ppm  5 (10) 10  31 ppm  5(10) 10  8 ppm  10 (50) 50  2 ppm  50 50  0 ppm 100 100

TABLE 15 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Compound (b) Compound No. 3 500 ppm 125 ppm 0 ppm 125 ppm  5 (10)  10 10 31 ppm  5 (10)  5 (10) 10  8 ppm  5 (50)  10 (50) 50  2 ppm  50  10(50) 50  0 ppm 100 100 100

TABLE 16 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Compound Cymoxanil No. 1 31 ppm 8 ppm 2 ppm 0 ppm    8 ppm  0 (7)  15(70)  85 70    2 ppm  2 (10)  15 (100)  85 (100) 100  0.5 ppm 10  50(100)  70 (100) 100 0.125 ppm  7 (10) 100 100 100    0 ppm 10 100 100100

TABLE 17 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Cymoxanil Compound No. 2 31 ppm 0 ppm 125 ppm  5 (7) 10  31 ppm  5 (7)10  8 ppm  5 (35) 50  2 ppm  5 (70) 100  0 ppm 70 100

TABLE 18 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Metalaxyl Compound No. 1 2 ppm 0.5 ppm 0 ppm    8 ppm 20 (42)  10 (70)70    2 ppm  7 (60)  70 (100) 100  0.5 ppm 35 (60)  85 (100) 100 0.125ppm 70 100 100    0 ppm 60 100 100

TABLE 19 Curative Effect on Cucumber Downy Mildew (Incidence Rate; %)Dimethomorph Compound No. 1 31 ppm 8 ppm 0 ppm   8 ppm  0 (35)  4 (42)70   2 ppm  4 (50) 50 (60) 100 0.5 ppm 20 (50) 85 100   0 ppm 50 60 100

TEST EXAMPLE 5 Test of Curative Effect on Cucumber Downy Mildew

A cucumber (cultivars: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis). After 18 hours, 20 ml of a compositioncontaining Compound No. 1 and compound (c)(3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione) inrespective concentrations shown in Table 20 was sprayed on two seedlingsby means of a spray gun. The plants were kept in a chamber set at 22 to24° C. for 5 days, and the average lesion area of the two seedlings wasobtained, from which the disease incidence rate (%) was calculated inthe same manner as in Test Example 1. The results obtained are shown inTable 20.

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parenthesis in Table 20.Theoretical incidence rate (%)=(X ⁴ ×Y ⁴)/100

wherein X⁴ is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y⁴ is an incidence rate (%) of a plant treated withonly compound (c). TABLE 20 Curative Effect on Cucumber Downy Mildew(Incidence Rate; %) Compound Compound (c) No. 1 800 ppm 400 ppm 200 ppm0 ppm 200 ppm 0 (4)  0 (13)  0 (48) 87 100 ppm 0 (5)  0 (14)  0 (52) 95 50 ppm 0 (5)  0 (14)  0 (52) 95  0 ppm 5 15 55 100

TEST EXAMPLE 6 Test of Curative Effect on Tomato Late Blight

A tomato (cultivar: Ponderosa) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a four-leaf stage, it wasinoculated by spraying a zoosporangium suspension of fungi of lateblight (Phytophthora infestans). After 6 hours, 10 ml/pot of acomposition containing Compound No. 1 and Cymoxanil, Metalaxyl orDimethomorph in the respective concentrations shown in Tables 21 to 23was sprayed on the plant by means of a spray gun. The plant was kept ina chamber set at 22 to 24° C. for 3 to 5 days, and the lesion area wasmeasured, from which the disease incidence rate (%) was calculated inthe same manner as in Test Example 1. The results obtained are shown inTables 21 to 23.

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Tables 21 to23.Theoretical incidence rate (%)=(X ⁵ ×Y ⁵)/100

wherein X⁵ is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y⁵ is an incidence rate (%) of a plant treated withonly Cymoxanil, Metalaxyl or Dimethomorph. TABLE 21 Curative Effect onTomato Late Blight (Incidence Rate; %) Compound Cymoxanil No. 1 2 ppm0.5 ppm 0 ppm 500 ppm  0 (10)  4 (10)  10 125 ppm  70 (85)  60 (85)  85 31 ppm  70 (100)  85 (100) 100  8 ppm  85 (100) 100 100  0 ppm 100 100100

TABLE 22 Curative Effect on Tomato Late Blight (Incidence Rate; %)Compound Metalaxyl No. 1 8 ppm 2 ppm 0.5 ppm 0 ppm 500 ppm  2  2  0 (7)10 125 ppm  0 (13)  2 (13) 10 (59) 85  31 ppm  7 (15)  7 (15) 20 (70)100  8 ppm  7 (15) 10 (15) 60 (70) 100  0 ppm 15 15 70 100

TABLE 23 Curative Effect on Tomato Late Blight (Incidence Rate; %)Compound Dimethomorph No. 1 31 ppm 8 ppm 0 ppm 500 ppm  0 (8.5)  0 (10)10 125 ppm  4 (72)  20 (85) 85  31 ppm 60 (85)  70 (100) 100  8 ppm 30(85) 100 100  0 ppm 85 100 100

TEST EXAMPLE 7 Field Test on Cucumber Downy Mildew

Seven cucumber seedlings (cultivar: Tokiwa Kohai Hikari No. 3, P type)were planted in a divided area 5 m² each) of the field located inKusatsu City, Shiga, Japan on May 9, 1995. A composition containingCompound No. 1 and Chlorothalonil in the respective concentrations shownin Table 24 below was sprayed over the plants in an amount of 500 to 750ml per area by means of a small-sized spraying machine on May 30 andJune 6. On June 14, all the leaves were observed to obtain a controlindex in accordance with the following rating system. The resultsobtained are shown in Table 24. Artificial infection with a pathogenicfungus was not conducted so that the disease was spontaneous. ControlIndex Severity of Disease 5 The lesion area or length is less than 7% ofthat of a control (non-treated area). 4 The lesion area or length is 7%or more and less than 10% of that of the control. 3 The lesion area orlength is 10% or more and less than 20% of that of the control. 2 Thelesion area or length is 20% or more and less than 30% of that of thecontrol. 1 The lesion area or length is 30% or more of that of thecontrol.

TABLE 24 Field Test on Cucumber Downy Mildew (Control Index)Chlorothalonil Compound No. 1 400 ppm 0 ppm 12.5 ppm 5 3   0 ppm 1 1

TEST EXAMPLE 8 Test of Preventive Effect on Cucumber Downy Mildew

A cucumber (cultivar: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, 10 ml of acomposition containing Compound No. 1 and Deutch Bordeaux A (trade nameof copper oxychloride wettable powder produced by Hokko ChemicalIndustry Co., Ltd.) in respective concentrations shown in Table 25 belowwas sprayed on the seedling by means of a spray gun. After 24 hours, itwas inoculated by spraying a spore suspension of fungi of dawny mildew(Pseudopernospora cubensis). The plant was kept in a chamber set at 22to 24° C. for 6 days, and the lesion area of the first leaf wasmeasured, from which the disease incidence rate (%) was calculatedaccording to the following formula. The results obtained are shown inTable 25.Incidence rate (%)=(a/b)×100wherein a is a lesion area of a treated plant; and b is a lesion area ofa control (non-treated plant).

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Table 25.Theoretical incidence rate (%)=(X ⁶ ×Y ⁶)/100

wherein X⁶ is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y⁶ is an incidence rate (%) of a plant treated withonly Duitch Bordeaux A. TABLE 25 Preventive Effect on Cucumber DownyMildew (Incidence Rate; %) Duitch Bordeaux A Compound No. 1 50 ppm 0 ppm 0.2 ppm  0 (7) 7 0.025 ppm  70 (100) 100    0 ppm 100 100

TEST EXAMPLE 9 Test of Preventive Effect on Tomato Late Blight

A tomato (cultivar: Ponderosa) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a four-leaf stage, 10 ml of acomposition containing Compound No. 1 and Kocide Bordeaux (trade name ofa cupric hydroxide wettable powder produced by Griffin) or DuitchBordeaux A (trade name of copper oxychloride wettable powder produced byHokko Chemical Industry Co., Ltd.) in the respective concentrationsshown in Tables 26 and 27 below was sprayed on the seedling by means ofa spray gun. After 24 hours, it was inoculated by spraying azoosporangium suspension of fungi of late blight (Phytophthorainfestans). The plant was kept in a chamber set at 22 to 24° C. for 3days, and the lesion area was measured, from which the disease incidencerate (%) was calculated in the same manner as in Test Example 1. Theresults obtained are shown in Tables 26 and 27.

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Tables 26 and27.Theoretical incidence rate (%)=(X ⁷ ×Y ⁷)/100

wherein X⁷ is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y⁷ is an incidence rate (%) of a plant treated withonly Kocide Bordeaux or Deutch Bordeaux A. TABLE 26 Preventive Effect onTomato Late Blight (Incidence Rate; %) Kocide Bordeaux Compound No. 1 50ppm 0 ppm 0.8 ppm  9 (47) 47 0.4 ppm  37 (50) 50   0 ppm 100 100

TABLE 27 Preventive Effect on Tomato Late Blight (Incidence Rate; %)Deutch Bordeaux A Compound No. 1 200 ppm 0 ppm   3 ppm  0 (31) 31 1.5ppm  3 (37) 37   0 ppm 100 100

TEST EXAMPLE 10 Test of Curative Effect on Cucumber Downy Mildew

A cucumber (cultivar: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis). After 24 hours, 10 ml of a compositioncontaining Compound No. 1 and aluminum tris(ethyl phosphonate)(Fosetyl-aluminum) in the respective concentrations shown in Table 28was sprayed onto the plant by means of a spray gun. The plant was keptin a chamber set at 22 to 24° C. for 6 days, and the lesion area of thefirst leaf was measured, from which the disease incidence rate (%) wascalculated in the same manner as in Test Example 1. The results obtainedare shown in Table 28.

A theoretical incidence rate (%) can be calculated from the followingColby's formula. In cases where an incidence rate of a testedcomposition is lower than the theoretical one, the tested compositioncan be the to produce a synergistic effect. In these cases, thetheoretical incidence rate (%) is shown in parentheses in Table 28.Theoretical incidence rate (%)=(X ⁸ ×Y ⁸)/100

wherein X⁸ is an incidence rate (%) of a plant treated with onlyCompound No. 1; and Y⁸ is an incidence rate (%) of a plant treated withonly Fosetyl-aluminum. TABLE 28 Curative Effect on Cucumber Downy Mildew(Incidence Rate; %) Compound Fosetyl-Aluminum No. 1 2000 ppm 500 ppm 0ppm 50 ppm 12.5 (48.8) 40 (55.3) 65  0 ppm 75 85 100

TEST EXAMPLE 11 Test of Curative Effect on Cucumber Downy Mildew

Preparation of Aqueous Dispersion:

A spreader (activity-enhancing ingredient) shown in Table 29 below was500-fold or 1000-fold diluted with water, and Compound No. 1 was addedthereto in a concentration of 100 ppm or 12.5 ppm to prepare an aqueousdispersion. For comparison, an aqueous dispersion containing 100 ppm or12.5 ppm of Compound No. 1 and containing no activity-enhancingingredient was prepared in the same manner.

Test Method and Results:

A cucumber (cultivar: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis). After 15 to 24 hours, the aqueousdispersion was sprayed over the plant with a spray gun in an amount of20 ml per 0.25 m². The plant was kept in a chamber set at 22 to 24° C.for 4 to 6 days, and the lesion area of the first leaf was measured toobtain a control index in accordance with the following rating system.The results obtained are shown in Table 29. Control Index Severity ofDisease 4 The lesion area or length is less than 20% of that of acontrol (non-treated plant). 3 The lesion area or length is 20% or moreand less than 40% of that, of the control. 2 The lesion area or lengthis 40% or more and less than 60% of that of the control. 1 The lesionarea or length is 60% or more of that of the control.

TABLE 29 Control Activity- Index enhancing Conc. of ingredient Compound(Spreader) No. 1 Dilution (ppm) No. Rate 100 12.5 1  500-fold — 4 2 500-fold — 4 3  500-fold — 4 4  500-fold 4 3 5  500-fold 4 3 6 500-fold 4 2 7  500-fold 4 4 8  500-fold 4 4 9  500-fold — 4 101000-fold 4 3 11  500-fold — 4 12  500-fold — 4 13  500-fold — 4 14 500-fold — 4 15  500-fold — 4 16  500-fold — 4 17  500-fold — 4 18 500-fold — 4 19  500-fold — 4 20  500-fold — 4 21  500-fold 3 — 22 500-fold — 4 23  500-fold — 4 25  500-fold — 4 26  500-fold 4 4 27 500-fold 4 4 28  500-fold — 4 29  500-fold — 4 30  500-fold — 4 31 500-fold — 4 32  500-fold — 4 33  500-fold — 4 34  500-fold — 4 35 500-fold — 4 36  500-fold 4 3 37  500-fold 4 4 38  500-fold 4 4 40 500-fold — 4 41  500-fold — 4 42  500-fold — 4 43  500-fold — 4 44 500-fold — 4 45  500-fold 4 3 46  500-fold — 4 47  500-fold — 4 48 500-fold 4 4 49  500-fold 4 3 50  500-fold 4 4 51  500-fold 4 4 52 500-fold 4 4 53  500-fold 4 4 54  500-fold 4 4 55  500-fold 4 4 56 500-fold — 4 57  500-fold 4 4 59  500-fold 4 4 60  500-fold 4 4 61 500-fold — 4 62  500-fold — 4 63  500-fold — 4 64  500-fold — 4 65 500-fold — 4 66  500-fold — 4 67  500-fold — 4 68 1000-fold — 4 70 500-fold — 4 71  500-fold — 4 72  500-fold 4 4 73  500-fold — 3 74 500-fold — 4 75  500-fold — 4 76  500-fold 4 4 77  500-fold 4 4 78 500-fold — 4 79  500-fold — 4 80  500-fold — 4 81  500-fold — 4 82 500-fold — 4 83  500-fold — 4 84  500-fold — 4 85  500-fold — 4 86 500-fold — 4 87  500-fold — 4 none 1 1

TEST EXAMPLE 12 Test of Curative Effect on Tomato Late Blight

Preparation of Aqueous Dispersion:

A spreader (activity-enhancing ingredient) shown in Table 30 below was500-fold diluted with water, and Compound No. 1 was added thereto in aconcentration of 400 ppm or 12.5 ppm to prepare an aqueous dispersion.

For comparison, an aqueous dispersion was prepared in the same manner,except for using a sorbitan fatty acid ester surface active agent shownin Table 30 below (comparative spreader A, B or C) as a spreader andadding Compound No. 1 in a concentration of 400 ppm. For furthercomparison, an aqueous dispersion containing 400 ppm or 12.5 ppm ofCompound No. 1 and containing no activity-enhancing ingredient wasprepared in the same manner. TABLE 30 Comparative Trade Name SpreaderKind Designation (Manufacturer) A polyoxyethylene polyoxyethyleneAPPLAUCH ® hexitan fatty hexitan fatty (Kao Corporation) acid ester acidester B polyoxyethylene polyoxyethylene Alsoap 30 hexitan fatty hexitanfatty (Sankei acid ester acid ester 50% Chemical Co., Ltd., TakedaChemical Industries, Ltd.) C polyoxyethylene oxysorbic Tween 20 (Wakosorbitan fatty polyoxyethylene Pure Chemical acid ester sorbitanIndustries, monolaurate Ltd.)Test Method and Results:

A tomato (cultivar: Ponderosa) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a four-leaf stage, it wasinoculated by spraying a zoosporangium suspension of fungi of lateblight (Phytophthora infestans). After 4 hours, the aqueous dispersionabove prepared was sprayed over the plant with a spray gun in an amountof 20 ml per 0.25 m After the plant was kept in a chamber set at 22 to24° C. for 3 days, the lesion area was measured, from which a controlindex was obtained in accordance with the same rating system as in TestExample 11. The results obtained are shown in Table 31. TABLE 31Curative Effect on Tomato Late Blight (Control Index) Control Activity-Index enhancing Conc. of ingredient Compound (Spreader) No. 1 Dilution(ppm) No. Rate 400 12.5  7 500-fold 3 — 19 500-fold 4 — 22 500-fold 3 —23 500-fold — 4 25 500-fold — 3 27 500-fold 3 — 35 500-fold 4 — 39500-fold — 4 42 500-fold — 4 43 500-fold — 4 46 500-fold — 3 55 500-fold3 — 61 500-fold 3 — 67 500-fold 4 — 76 500-fold 3 — 88 500-fold — 3 90500-fold — 4 Comparative A 500-fold 2 — B 500-fold 2 — C 500-fold 2 —none 1 1

TEST EXAMPLE 13 Test of Curative Effect on Tomato Late Blight

Preparation of Aqueous Dispersion:

A spreader (activity-enhancing ingredient) shown in Table 32 below was2000-fold diluted with water, and Compound No. 1 was added thereto in aconcentration of 100 ppm to prepare an aqueous dispersion. Forcomparison, an aqueous dispersion containing 100 ppm of Compound No. 1and containing no activity-enhancing ingredient was prepared in the samemanner.

Test Method and Results:

A tomato (cultivar: Ponderosa) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a four-leaf stage, it wasinoculated by spraying a zoosporangium suspension of fungi of lateblight (Phytophthora infestans). After 4 hours, the aqueous dispersionabove prepared was sprayed over the plant with a spray gun in an amountof 20 ml per 0.25 m². After the plant was kept in a chamber set at 22 to24° C. for 3 days, the lesion area was measured, from which a controlindex was obtained in accordance with the same rating system as in TestExample 11. The results obtained are shown in Table 32. TABLE 32Curative Effect on Tomato Late Blight (Control Index) Activity-enhancingingredient No Activity- Spreader No. enhancing 23 24 39 88 90 ingredientControl Index 4 4 4 4 4 2

TEST EXAMPLE 14 Test of Preventive Effect on Tomato Late Blight

Preparation of Aqueous Dispersion:

Spreader No. 58 or 91 (activity-enhancing ingredient) was 500-folddiluted with water, and Compound No. 1 was added thereto in a prescribedconcentration to prepare an aqueous dispersion. For comparison, anaqueous dispersion containing the same concentration of Compound No. 1and containing no activity-enhancing ingredient was prepared in the samemanner.

Test Method and Results:

A tomato (cultivar: Ponderosa) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a four-leaf stage, theaqueous dispersion above prepared was sprayed over the plant with aspray gun in an amount of 20 ml per 0.25 m². After 24 hours from thespray treatment, a zoosporangium suspension of fungi of late blight(Phytophthora infestans) was sprayed for inoculation, and the plant waskept in a chamber set at 22 to 24° C. for 3 days. The lesion area wasmeasured, from which a control index was obtained in accordance with thesame rating system as in Test Example 11. The results obtained are shownin Table 33. TABLE 33 Preventive Effect on Tomato Late Blight (ControlIndex) Activity-enhancing ingredient Spreader No. Spreader No. Compound58 (500-fold 91 (500-fold No. 1 diluted) diluted) None 1.6 ppm 4 4 3 0.8ppm 4 4 1 0.4 ppm 1 3 1

TEST EXAMPLE 15 Test of Curative Effect on Cucumber Downy Mildew

Preparation of Aqueous Dispersion:

A spreader (activity-enhancing ingredient) shown in Table 34 below was500-fold or 2000-fold diluted with water, and Compound No. 1 was addedthereto in a concentration of 12.5 ppm to prepare an aqueous dispersion.For comparison, an aqueous dispersion containing 12.5 ppm of CompoundNo. 1 and containing no activity-enhancing ingredient was prepared inthe same manner.

Test Method and Results:

A cucumber (cultivar: Suyo) was cultivated in polyethylene pots(diameter: 7.5 cm). When the plant reached a two-leaf stage, it wasinoculated by spraying a spore suspension of fungi of downy mildew(Pseudoperonospora cubensis) After 15 to 24 hours, the aqueousdispersion was sprayed over the plant with a spray gun in an amount of20 ml per 0.25 m². The plant was kept in a chamber set at 22 to 24° C.for 5 days, and the lesion area of the first leaf was measured to obtainthe lesion-free area ratio (%). The results obtained are shown in Table34. TABLE 34 Curative Effect on Cucumber Downy Mildew (Lesion-free AreaRatio; %) Dilution Ratio of Activity- enhancing Spreader No. ingredient23 24 39 88 89 90 none  500-fold 100 100 100 95 90 100 65 2000-fold 100100 100 83 — 95(note: all parts on the following Formulation Examples 1-14 andReference Formulation Example are indicated by weight.)

FORMULATION EXAMPLE 1

(1) Compound No. 1 5 parts (by weight, hereinafter the same) (2)Dipotassium hydrogenphosphate 7 parts (3) Diatomaceous earth 82 parts (4) Dialkyl sulfosuccinate 2 parts (5) Polyoxyethylene alkylphenyl ethersulfate 4 parts

The above components were mixed uniformly to obtain a wettable powder.

FORMULATION EXAMPLE 2

(1) Compound No. 1 5 parts (2) Sodium tertiary phosphate dodecahydrate16 parts  (3) Diatomaceous earth 73 parts  (4) Dialkyl sulfosuccinate 2parts (5) Polyoxyethylene alkylphenyl ether sulfate 4 parts

The above components were mixed uniformly to obtain a wettable powder.

FORMULATION EXAMPLE 3

(1) Compound No. 1  5 parts (2) Dipotassium hydrogenphosphate 18 parts(3) Kerosene 63 parts (4) Dialkyl sulfosuccinate  2 parts (5) Mixture ofpolyoxyethylene phenylphenol 12 parts derivative and polyoxyethylenesorbitan alkylate

The above components were mixed uniformly and finely ground to obtain asuspension concentrate.

FORMULATION EXAMPLE 4

(1) Kaolin 78 parts (2) Sodium β-naphthalenesulfonate-formaldehyde  2parts condensate (3) Polyoxyethylene alkylaryl sulfate  5 parts (4)Hydrated amorphous silicon dioxide 15 parts

A mixture of the above components, dipotassium hydrogenphosphate, andCompound No. 1 were mixed at a weight ratio of 79:20:1 to obtain awettable powder.

FORMULATION EXAMPLE 5

(1) Kaolin 78 parts (2) Sodium β-naphthalenesulfonate-formaldehyde  2parts condensate (3) Polyoxyethylene alkylaryl sulfate  5 parts (4)Hydrated amorphous silicon dioxide 15 parts

A mixture of the above components, Compound No. 1, and Metalaxyl weremixed at a weight ratio of 8:1:1 to obtain a wettable powder.

FORMULATION EXAMPLE 6

(1) Compound No. 2 0.5 part (2) Metalaxyl 0.5 part (3) Bentonite 20parts (4) Kaolin 74 parts (5) Sodium lignin sulfonate 5 parts

The above components were mixed together with an adequate amount ofwater enough for granulation, followed by granulation to obtaingranules.

FORMULATION EXAMPLE 7

(1) Compound No. 3 0.25 part (2) Metalaxyl 0.25 part (3) Calciumcarbonate 99.0 parts (4) Lower alcohol phosphate 0.5 part

The above components were mixed uniformly to obtain a dust.

FORMULATION EXAMPLE 8

(1) Kaolin 78 parts (2) Sodium β-naphthalenesulfonate-formaldehyde  2parts condensate (3) Polyoxyethylene alkylaryl sulfate  5 parts (4)Hydrated amorphous silicon dioxide 15 parts

A mixture of the above components, Compound No. 1, and Kocide Bordeaux(trade name) were mixed at a weight ratio of 0.8:76.8:22.4 to obtain awettable powder.

FORMULATION EXAMPLE 9

(1) Kaolin 78 parts (2) Sodium β-naphthalenesulfonate-formaldehyde  2parts condensate (3) Polyoxyethylene alkylaryl sulfate  5 parts (4)Hydrated amorphous silicon dioxide 15 parts

A mixture of the above components, Compound No. 1, and Duitch Bordeaux A(trade name) were mixed at weight ratio of 5:67.2:27.8 to obtain awettable powder.

FORMULATION EXAMPLE 10

(1) Compound No. 1 0.25 part (2) Sanpun Bordeaux Dust DL (trade name,0.25 part produced by Dai-ichi Noyaku K.K. and Hokko Chemical IndustryCo., Ltd.) (3) Sodium carbonate 99.0 parts (4) Lower alcohol phosphate0.5 part

The above components were mixed uniformly to obtain a dust.

FORMULATION EXAMPLE 11

(1) Compound No. 1 0.5 part (2) Sanpun Bordeaux Dust DL (trade name, 0.5part produced by Dai-ichi Noyaku K.K. and Hokko Chemical Industry Co.,Ltd.) (3) Bentonite 20 parts (4) Kaolin 74 parts (5) Sodium ligninsulfonate 5 parts

The above components were mixed together with an adequate amount ofwater enough for granulation, followed by granulation to obtaingranules.

FORMULATION EXAMPLE 12

(1) Compound No. 1 5 parts (2) Aluminum tris(ethyl phosphonate) 5 parts(Fosetyl-aluminum) (3) Diatomaceous earth 84 parts  (4) Calcium ligninsulfonate 2 parts (5) Dialkyl sulfosuccinate 4 parts

The above components were mixed uniformly to obtain a wettable powder.

FORMULATION EXAMPLE 13

(1) Compound No. 1 (active ingredient) 11.1 parts (2) DispersantSOPROPHOR FLK (trade name, 1.1 part produced by RHôNE-POULENC) (3)Dispersing and wetting agent Supragil 1.1 part MNS/90 (trade name) (4)Dispersing and suspending agent Vegum 1.7 parts (5) Urea (acting as anantifreezing agent) 11.1 parts (6) Antifoaming agent SM5572F (tradename) 0.1 part (7) Distilled water 73.8 parts

The above components (1) to (7) were mixed and wet ground until theactive ingredient had an average particle size of 2 μm to prepare asuspension. To 90 parts of the resulting suspension was added 10 partsof an activity-enhancing ingredient, followed by mixing by shaking toprepare an aqueous suspension concentrate.

FORMULATION EXAMPLE 14

(1) Compound No. 1 (active ingredient) 10.0 parts (2) DispersantSOPROPHOR FLK (trade name, 1.0 part produced by PHôNE-POULENC) (3)Dispersing and wetting agent Supragil 1.0 part MNS/90 (trade name) (4)Dispersing and suspending agent Vegum 1.5 parts (5) Urea (acting as anantifreezing agent) 10.0 parts (6) Antifoaming agent SM5572F (tradename) 0.1 part (7) Distilled water 66.4 parts (8) Activity-enhancingingredient 10.0 parts

The above components (1) to (8) were mixed and wet ground until theactive ingredient had an average particle size of 2 μm to prepare anaqueous suspension concentrate.

REFERENCE FORMULATION EXAMPLE

(1) Kaolin 78 parts (2) Sodium β-naphthalenesulfonate-formaldehyde  2parts condensate (3) Polyoxyethylene alkylaryl sulfate  5 parts (4)Hydrated amorphous silicon dioxide 15 parts

A mixture of the above components and an inorganic phosphorous compoundat a weight ratio of 4:1 to prepare a 20% wettable powder of theinorganic phosphorous compound.

INDUSTRIAL APPLICABILITY

The compositions for controlling harmful bio-organisms according to thepresent invention have high curative and/or preventive effects on cropplants suffering from plant diseases caused by harmful bio-organisms andcan control the harmful bio-organisms. In particular, the compositionscontaining the activity-enhancing ingredient exhibit enhanced curativeeffects so that the amount of the active ingredient can be reduced.

While the invention has been described in detail and with reference tospecific embodiments thereof, it will be apparent to one skilled in theart that various changes and modifications can be made therein withoutdeparting from the spirit and scope thereof.

1-20. (canceled)
 21. A composition for controlling harmful bio-organismscomprising (a) at least one imidazole compound represented by formula(I):

wherein R represents a lower alkyl group or a lower alkoxy group; and nrepresents an integer of 1 to 5, as an active ingredient, and (b) atleast one fungicide for Phycomycetes which is at least one memberselected from the group consisting of a β-methoxyacrylate compound, anoxazolidinedione compound, a cinnamic acid compound and a coppercompound as an active ingredient.
 22. The composition according to claim21, wherein the fungicide is a compound selected from the groupconsisting of: methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl (E)-methoxyimino[α-(o-tolyloxy)-O-tolyl]acetate,3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione, methylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate,2-methoxy-N-(2-oxo-1,3-oxazolidin-3-yl)aceto-2′,6′-xylidide,(±)-α-2-chloro-N-(2,6-xylylacetamide)-γ-butyrolactone, methylN-phenylacetyl-N-(2,6-xylyl)-DL-alaninate, methylN-(2-furoly)-N-(2,6-xylyl)-DL-alaninate,(±)-α-[N-(3-chlorophenyl)cyclopropane-carboxamide]-γ-butyrolactone,(E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylolyl]morpholine,an inorganic copper fungicide and an organic copper fungicide.
 23. Thecomposition according to claim 21, wherein the fungicide is a compoundselected from the group consisting of: methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidine-4-yloxyl]phenyl}-3-methyoxyacrylate,methyl (E)-methyoxyimino[α-(o-tolyloxy)-O-tolyl]acetate,3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione, methylN-(2-methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate,(E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylolyl]morpholineand an inorganic copper fungicide.
 24. The composition according toclaim 21, wherein the imidazole compound and the fungicide are at aweight ratio of 1:10,000 to 10,000:1.